The present invention is directed to a novel process for the production of .alpha.-chloro-.alpha.-oximino-4-hydroxyacetophenone.
.alpha.-chloro-.alpha.-oximino-4-hydroxyacetophenone is known and has the structural formula (I): ##STR1## The preparation thereof has been described in the literature, for example, by N. Levin and W. H. Hartong, Journal of Organic Chemistry, (1942), 7,408. Preparation involves reacting hydroxyphenacyl chloride with isopropyl nitrite in the presence of hydrogen chloride to yield the product. The reaction can be depicted as in equation (II): ##STR2##
.alpha.-chloro-.alpha.-oximino-4-hydroxyacetophenone is known to have good antibacterial and germicidal properties. Thus, the compound has found use as an industrial biocide to control the growth of bacteria and microorganisms which develop in water-based media used in the manufacture of various industrial products. Discovery of the antibacterial and germicidal properties of .alpha.-chloro-.alpha.-oximino-4-hydroxyacetophenone is described in British Pat. No. 1,290,646. For use as an industrial biocide, the active ingredient is used in association with a suitable vehicle. Suitable vehicles include water, alcohols, hydrocarbons and other organic solvents as well as mineral, animal and vegetable oils. The compositions typically contain upwards of 10-20% by weight of the active ingredient.
While the previous method of forming .alpha.-chloro-.alpha.-oximino-4-hydroxyacetophenone has been useful, the starting hydroxyphenacyl chloride is disadvantageous in view of its cost and, because it is a solid, it is difficult to handle. Also, hydroxylphenacyl chloride is a strong lachrymater and causes severe dermatitis.
Accordingly, it would be worthwhile to provide a new process for the production of .alpha.-chloro-.alpha.-oximino-4-hydroxyacetophenne, in particular, a process that would use a starting material which is less expensive and easier to handle than hydroxyphenacyl chloride. Thus, the primary objective of the present invention is to provide such a novel process for the production of .alpha.-chloro-.alpha.-oximino-4-hydroxyacetophenone.